SU583738A3 - Method of preparing derivatives of 4-phenyl-2-methyl-1-carboxylic acid - Google Patents

Method of preparing derivatives of 4-phenyl-2-methyl-1-carboxylic acid

Info

Publication number
SU583738A3
SU583738A3 SU7201785408A SU1785408A SU583738A3 SU 583738 A3 SU583738 A3 SU 583738A3 SU 7201785408 A SU7201785408 A SU 7201785408A SU 1785408 A SU1785408 A SU 1785408A SU 583738 A3 SU583738 A3 SU 583738A3
Authority
SU
USSR - Soviet Union
Prior art keywords
chj
methyl
phenyl
carboxylic acid
preparing derivatives
Prior art date
Application number
SU7201785408A
Other languages
Russian (ru)
Inventor
Франке Альбрехт (Фрг)
Трабер Вальтер (Швейцария)
Original Assignee
Циба-Гейги Аг (Фирма)
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from CH720571A external-priority patent/CH551742A/en
Application filed by Циба-Гейги Аг (Фирма) filed Critical Циба-Гейги Аг (Фирма)
Application granted granted Critical
Publication of SU583738A3 publication Critical patent/SU583738A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

Реакцию провод т в инертных относитель но реагентов растворител х и разбавител х, например в углеводородах ароматического р да, таких, как бензол толуол, ксилол, в спиртах метаноле, этаноле, пропаноле, изопропаноле или в бутанолах, гликол х, афирах, таких; как диизопропиловый эфир, тет агидрофуран, диоксан, или в -/ЗИ йлкилироваиных аминах, например в диа№ килформамиде, в сульфоксиде, Д етилггар ролидоне . Температура реакции от О до 150 С. П р и м е р . В смесь 816 г дифенил ирго эфира, 3,5 кг концентрированной сол рной кислоты и 520 г 36%-ного раствора формальдегида при ,перемешивании в течение 16 часВВОДЯТ при с хлористый водород. Затем раствор вылпваюг в лед ную ЙОДУ и экстрагируют смесью диэтиловыЕ эфир петрвлейный эфир. Органическую несколько раз Промывают водой высу Шйвают, добавл  -небольшое количество карбоната кали , над сульфатом натри  и упаривают. Остаток перегон ют в вакууме с добавлением карбоната кали . При 143 is 6 С и давлении 2 мм рт ст. получает чистый хлористый феноксибепзвл, J.6,1 Гт натри  pacTBOpSiior в 400 мл абсолютного этанола н в еще гор чий раст аор в течение 1 час .прикапывают 182 г этилового эфира ацетоуксусной кислоты, посЦ л0 чего при температуре кипени  добавлшот по капл м в течение 3 час 156 г хлориатого феноксибенаила. Смесь кигг т т с обра ным холодильником еще 15 час, фильтруют после охлаждени , удал  белыЙ осадок, и раствор упаривают, К остатку добавл ют 100 г едкого натра.в 2 л водыг смесь пе ремешивают 15 час при температуре шш, а затем экстрагируют диэтиловым эфиром. Органические фазы высушивают н упаривают, После дистилл ции в глубоком вакууме получают 4-(4-феноксифенил)-2«-бутанол , т. кип 144,5-148 С/О,03 мм рт,с К взвеси35 г безводного хлористого алюмини  в 100 мл сухого хлористого МЭтплена при 1О-20 С прикапывают 34 г ди фенилового эфира, раствореннохо в 100 ъ/ш cyjsoro холористого метилена. Затем в те Нение ЗО мин в смесь ввод т, изредка олла дай, при 15-20 С 14 г метилвинилкетона в 50 мл хлористого метилена, после чего реакционную взвесь перемешивают 2,5 час при 5-10 С и выливают в 1 л лед1гаой воды . Далее с помощью концентрированной сол ной кислоты довод т взвесь до сильно кислой реашщи, раствор хлористого метилена отдел ют, а оставшуюс  водную взвесь трижды экстрагируют хлористым метиленом по 100 мл. Соединенные экстракты хлористого-метилена трижды промывают водой по 400 мл до нейтральной реакции, высушивают над сульфатом натри  и отфильтровывают . После отгонки хлористого метилена получают 46,3 г зеленого масла, которое фракционируют в глубоком вакууме. Получают 23 г 4(4- феноксифенил)-бутанона, т, кип, 135-136 С/О,001 мм рт. ст,, 1,5648, В смесь 24 г 4-( 4-феноксифенил)-бута иЬна , 7,2 г приблизительно 50%-ного гидр1 да натри  и 750 мл абсолютного бензола при комнатной температуре медленно прикапывают 30 г метилового эфира диметоксифосфинилуксусмой кислоты. При этом образуетс  сера  гелеобразна  масса, которую перемешивают еще 15 юc. Затем добавл ют 50О мл очень чистого диметилформам да и перемешивают еще 4 час. Смесь вы йвают в воду и экстрагируют диэтиловым Эфиром; органическутр фазу промывают еще несколько раз водой, высушивают над сулв фатом натри  и упаривают. Остаток хроматографируют на приблизительно ЗОО г силикагел , примен   в качестве элюента бен зол. Получают смесь цис и транс-соединений обшей формулы. Cff -CH3-(l CH-COOCH3 После повторногэ хроматографировани  на силикагеле с использованием в качестве адюента оме си бензол-чтетролейный эфир (1:1) получают 1/3 чистых цис-соединений и 2/3 чистых транс-соединений общих формул. CMj Ч1С 3/ b Cfb-C CM-COOCH5 . 140 150°C/Os001 мм рт. ст.) /-o- -dH;rCH,-c CH-coocHj ( n2jj° 1. 5638 ) Аналогично получают соединени , приведенные в таблице.The reaction is carried out in inert relative to the reagents solvents and diluents, for example, in aromatic hydrocarbons, such as benzene, toluene, xylene, in alcohols methanol, ethanol, propanol, isopropanol or in butanols, glycols, esters such; as diisopropyl ether, tetrahydrofuran, dioxane, or in - / ZI or alkyl amines, for example, in diamylformamide, in sulfoxide, D etylggar rolidone. The reaction temperature is from 0 to 150 ° C. PRI me R. Into a mixture of 816 g of diphenyl ether, 3.5 kg of concentrated hydrochloric acid and 520 g of a 36% formaldehyde solution with stirring for 16 hours, are introduced with hydrogen chloride. The solution was then poured into ice-iodine and extracted with diethyl ether ether. Organic several times. Washed with water. Sewed by adding a small amount of potassium carbonate, over sodium sulfate and evaporated. The residue is distilled in vacuo with the addition of potassium carbonate. At 143 is 6 C and a pressure of 2 mm Hg. receives pure phenoxybenzyl chloride, J.6.1 Gt of sodium pacTBOpSiior in 400 ml of absolute ethanol and hot solution for 1 hour. 182 g of ethyl acetoacetate are added dropwise, POC n0 which is added dropwise at boiling point 3 hours 156 g of chlorinated phenoxybenyl. A mixture of kiggs and a fridge is left for another 15 hours, filtered after cooling, the white precipitate is removed, and the solution is evaporated. 100 g of sodium hydroxide are added to the residue. In 2 liters of water, the mixture is stirred for 15 hours at a temperature of shm and then extracted with diethyl by ether. The organic phases are dried and evaporated. After distillation under high vacuum, 4- (4-phenoxyphenyl) -2'-butanol is obtained, i.p. 144.5-148 C / O, 03 mm Hg, K suspension 35 g of anhydrous aluminum chloride in 100 ml of dry methanol chloride at 10 ° -20 ° C are added dropwise with 34 g of di-phenyl ether, dissolved in 100 h / w cyjsoro of methylene chloride. Then, in the course of the DZ min, the mixture is introduced, occasionally melt, at 15–20 ° C, 14 g of methyl vinyl ketone in 50 ml of methylene chloride, after which the reaction suspension is stirred for 2.5 hours at 5–10 ° C and poured into 1 liter of ice water . Then, using concentrated hydrochloric acid, the suspension is adjusted to a strongly acidic solution, the methylene chloride solution is separated, and the remaining aqueous suspension is extracted three times with 100 ml of methylene chloride. The combined methylene chloride extracts are washed three times with 400 ml of water until neutral, dried over sodium sulfate and filtered. After distilling off the methylene chloride, 46.3 g of green oil are obtained, which are fractionated under high vacuum. 23 g of 4 (4-phenoxyphenyl) -butanone are obtained, t, bale, 135-136 C / O, 001 mm Hg. St ,, 1,5648, Into a mixture of 24 g of 4- (4-phenoxyphenyl) -but, 7.2 g of approximately 50% hydrogen and sodium, and 750 ml of absolute benzene, 30 g of dimethoxyphosphinylacetic acid methyl ester are slowly added dropwise at room temperature . Sulfur is formed as a gelatinous mass, which is stirred for another 15 ° C. Then, 50 O ml of very pure dimethyl forms is added and mixed for another 4 hours. The mixture is taken up in water and extracted with diethyl ether; The organic phase is washed several times with water, dried over sodium sulfate and evaporated. The residue is chromatographed on approximately ZOO g silica gel, using benzene as eluent. A mixture of cis and trans compounds of the general formula is obtained. Cff -CH3- (l CH-COOCH3 After repeated chromatography on silica gel using ohiobium benzene-1-ether ether (1: 1) as an additive), 1/3 of the pure cis compounds and 2/3 of the pure trans compounds of the general formulas are obtained. CMj CH1C 3 / b Cfb-C CM-COOCH5. 140 150 ° C / Os001 mmHg) / -o- -dH; rCH, -c CH-coocHj (n2jj ° 1. 5638) Similarly, the compounds given in the table.

,Формупа соецинени Formup Soicineni

СИ, Hi-CH,-( dff-d()OdHjSI, Hi-CH, - (dff-d () OdHj

СН, ()Н,-СНг(-СН-еов€Н5CH, () N, -СНг (-СН-еов € Н5

н, CHj-dH,- с -CH-ComttHs),n, CHj-dH, - with -CH-ComttHs),

CHjCHj

II

C-CH-COOCaHj СИ, C-CH-COOCaHj SI,

СИ, SI,

O- CHf-CHa-C-CH-deH сн,O-CHf-CHa-C-CH-deH,

(- H- JO-ll{,H5)2(- H-JO-ll {, H5) 2

л 20 Рl 20 r

1,5782 1,52951.5782 1.5295

1,525O1,525O

1,55631.5563

160-170160-170

1,5737 1,56001.5737 1.5600

CH.j-dHf-c-CH-cooCHjCH.j-dHf-c-CH-cooCHj

ЧС/СES / S

-eHj- H,-C-CH- eedKj-eHj- H, -C-CH- eedKj

, ,

«HI"HI

-j(b y-CHj-CJIj-e-CH-eeif-j (b y-CHj-CJIj-e-CH-eeif

CHjCHj

-CHj-CHj-C-CH-dO-UJdjflj)-CHj-CHj-C-CH-dO-UJdjflj)

nt/HtHCnt / HtHC

Cfls -CHj-CH C CH-CeOdnjCfls -CHj-CH C CH-CeOdnj

CHCH

/  /

CHjCHj

% -сНгЧ -сн,-сн,-с Сн-С5Т(% -NHC -Sn, -Sn, -sSn-C5T (

CHjCHj

HV-CHf- VCHj-CHj-C-CH-COeCH,HV-CHf-VCHj-CHj-C-CH-COeCH,

CHjCHj

wpewf ,-C CH-Cee H,wpewf, -C CH-Cee H,

1,58701.5870

1,59181.5918

1,60811.6081

1,55861.5586

1,55871.5558

1,57381.5738

1,52521.5252

1,58O41.58O4

Формуг а соеп.инени  Г CHj-С°(Н.-И трене Bf Вг-4 0- Cn-j-CK -C flH-fiO-lfCjH 4UC ,-сн с сн-б§ое ( CjHj- о CHj ИИ,-С СИ-СО В(СгН тра с CjHjО -flfl-j- OHf С СН-ЙООСНз Cfij-O- CH -CH C CH-COOCHj -CHf-(iH,(;ooCjtf -H иые rfiflaн 3-4 )-fHrCH,C CH-C09C5HT- 3C. цис: .аыс 3 :8 .,CK.j-C PH-COOC4H9--u3a aaf . т fane I i CHf-Cii -C Cn-COOC Hg-i Ss ( HUf : mfOfli 3 «H, . ЯСГЧy-EJVI . ° 9 СИ- mpoMC 3-2 V- CHj-O CHf-dtH-eoocHj VV-€H,- e ,-сп,-с йн-СййFormulag connection of CHj-C ° (N.-And tren Bf Br-4 0-Cn-j-CK -C flH-fiO-lfCjH 4UC, -sn with sn-bgoe (CjHj- o CHj II , -C SI-CO B (CgN tra with CjHjO -flfl-j-OHf C CH-YOOCH3 Cfij-O-CH-CH C CH-COOCHj-CHf- (iH, (; ooCjtf -H and rfiflan 3-4) -fHrCH, C CH-C09C5HT-3C. cis: .ays 3: 8., CK.jC PH-COOC4H9 - u3a aaf. tfane I i CHf-Cii -C Cn-COOC Hg-i Ss (HUf: mfOfli 3 "H,. YAKHCHY-EJVI. ° 9 SI-mpoMC 3-2 V-CHj-O CHf-dtH-eoocHj VV- € H, - e, -sp, -s yn-Syy

Продогикение таблицыProgress Table

2020

Tl 1.93 ,5705 ,5528 55-50 , 5642 s519e з5832 s5573 155-162 I,52fi6 1.5342Tl 1.93, 5705, 5528 55-50, 5642 s519e з5832 s5573 155-162 I, 52fi6 1.5342

99

Формула соединени Compound formula

f nVcH,-0-- rV-CHj-CM{-C CI -CON(C.,H5)zf nVcH, -0-- rV-CHj-CM {-C CI -CON (C., H5) z

СИ.SI.

/- / -

OlV-0 .H,-CHj-C lH-(OlV-0 .H, -CHj-C lH- (

COOdH,COOdH,

гg

AiV n-4, AiV n-4,

CHjCHj

/;A Q Q CH2-CHfC CH-conir Hsl2/; A Q Q CH2-CHfC CH-conir Hsl2

CH, CHf CH -S- jy-CHj-CHj-C CH-COOCH,CH, CHf CH -S-jy-CHj-CHj-C CH-COOCH,

-CHj-CHj-S- CHj-CHf C CH-CONlCjHsJj-CHj-CHj-S-CHj-CHf C CH-CONlCjHsJj

CHj H ) Д 7- СН-СООСН,CHj H) D 7-CH-SOOCH,

«Hj Vy-S- CHi-0,H.rC CH-CON(C2Hj)j"Hj Vy-S-CHi-0, H.rC CH-CON (C2Hj) j

CH, CHj 8- CHj-CH2-C CH-OOOC«jCH, CHj 8-CHj-CH2-C CH-OOOC “j

CHj -OH -S- CHj-CH -c CH-dooCHjCHj -OH -S- CHj-CH -c CH-dooCHj

ll

,o 5H,i-o-Q-o-(),-c(;H-(oo()Hj, o 5H, i-o-Q-o - (), - c (; H- (oo () Hj

-C Hg-O- O- CHj-CHfCCH-CffOCHj-C Hg-O- O-CHj-CHfCCH-CffOCHj

CHj-CHj y-o- CH2-CH -c CH- :oocHjCHj-CHj y-o- CH2-CH -c CH-: oocHj

CHjf HjCHjf Hj

/ /

0- -CH2-{H.j-C CH-COOC2H5 0- -CH2- {H.j-C CH-COOC2H5

CH,-CHjCH, -CHj

/ /

-0- -СН,-СНз-С CH-C EK-0- -СН, -СНз-С CH-C EK

CHj- Hj-CHjCHj- Hj-CHj

o- CHj-CH-fC ca-cooCHso- CHj-CH-fC ca-cooCHs

CHj-CHj-CHj -0 - V-CH2-CH.fC(H-COOC7H5CHj-CHj-CHj-0 - V-CH2-CH.fC (H-COOC7H5

CHj-CH,-CHj CHj-CH, -CHj

0 - -eHj-CH,-c cH-CEW0 - -eHj-CH, -c cH-CEW

583738583738

lOlO

Проаоггжение габпицыGabbica augmentation

2020

пP

1,5282 1,5292 1,53921.5282 1.5292 1.5392

1,53201.5320

1,5803 1,5761 1,5555 1,55481,5803 1,5761 1,5555 1,5548

1,5883 1,55231.5883 1.5523

1,54751.5475

1,5497 1671.5497 167

ff

168-174 174-178 1,5483 1,5427168-174 174-178 1,5483 1,5427

1,56091.5609

SU7201785408A 1971-05-15 1972-05-12 Method of preparing derivatives of 4-phenyl-2-methyl-1-carboxylic acid SU583738A3 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH720571A CH551742A (en) 1971-05-15 1971-05-15 4-phenyl-2-methyl-1-butene-1-carboxylic acid derivs - prepd by reacting phenoxyphenylbutanone with phosphinic acid,ester hormonal
CH508772 1972-04-06

Publications (1)

Publication Number Publication Date
SU583738A3 true SU583738A3 (en) 1977-12-05

Family

ID=25696946

Family Applications (1)

Application Number Title Priority Date Filing Date
SU7201785408A SU583738A3 (en) 1971-05-15 1972-05-12 Method of preparing derivatives of 4-phenyl-2-methyl-1-carboxylic acid

Country Status (17)

Country Link
US (1) US3824274A (en)
AT (1) AT317611B (en)
BE (1) BE783389A (en)
BG (1) BG21365A3 (en)
CA (1) CA996947A (en)
DD (1) DD97540A5 (en)
DE (1) DE2223380A1 (en)
ES (1) ES402748A1 (en)
FR (1) FR2137808B1 (en)
GB (1) GB1365446A (en)
HU (1) HU164586B (en)
IL (1) IL39387A (en)
IT (1) IT955489B (en)
NL (1) NL7206445A (en)
RO (1) RO68997A (en)
SE (1) SE377113B (en)
SU (1) SU583738A3 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4069344A (en) * 1972-05-10 1978-01-17 Ciba-Geigy Corporation Insecticidal substituted phenyl derivatives
IT1060551B (en) * 1974-06-10 1982-08-20 Lorenzini Sas Inst Biochim SUBSTITUTED AMID STARS OF 3-METHYL 4-PENYL 3 BUTENOIC ACID HAVING HIGH LIPOLIPEMIZING ACTION
GB1479297A (en) * 1974-07-04 1977-07-13 Beecham Group Ltd 4-substituted butan-2-ones but-3-en-2-ones butan-2-ols and but-3-en-2-ols and pharmaceutical compositions containing them
CA1137506A (en) * 1978-03-17 1982-12-14 Ulf Fischer Carbamic acid derivatives
US4855086A (en) * 1982-10-15 1989-08-08 Burroughs Wellcome Co. Novel pesticides, preparation and use
US4752616A (en) * 1987-06-29 1988-06-21 E. R. Squibb & Sons, Inc. Arylthioalkylphenyl carboxylic acids, compositions containing same and method of use

Also Published As

Publication number Publication date
DD97540A5 (en) 1973-05-12
NL7206445A (en) 1972-11-17
ES402748A1 (en) 1975-11-01
FR2137808B1 (en) 1980-04-18
HU164586B (en) 1974-03-28
IT955489B (en) 1973-09-29
SE377113B (en) 1975-06-23
RO68997A (en) 1982-02-26
US3824274A (en) 1974-07-16
BG21365A3 (en) 1976-05-20
BE783389A (en) 1972-11-13
CA996947A (en) 1976-09-14
IL39387A0 (en) 1972-07-26
AT317611B (en) 1974-09-10
DE2223380A1 (en) 1972-11-30
GB1365446A (en) 1974-09-04
IL39387A (en) 1975-04-25
FR2137808A1 (en) 1972-12-29

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